Jon Cryer

Cemented forever in the minds of teenage girls as the lovelorn Phil "Duckie" Dale in "Pretty in Pink" (1986), actor and writer Jon Cryer would years later attain a mature kind of fame as uptight Alan Harper on the hit sitcom, "Two and a Half Men" (CBS, 2003-15). In between those career-defining projects, Cryer had a number of wide-ranging roles, playing supervillain Lenny Luther in "Superman IV: The Quest for Peace" (1987) and a Wall Street broker avoiding the mob in "Hiding Out" (1987).

After starring as the titular character on the short-lived cult series "The Famous Teddy Z" (CBS, 1989-1990), he first crossed paths with future "Two and a Half Men" co-star Charlie Sheen on the spoof comedy "Hot Shots!" (1991). Meanwhile, Cryer continued a professional collaboration with Jennifer Tilly by appearing opposite her in the caper comedy "Heads" (1993), before co-starring with the actress in his screenwriting debut, "The Pompatus of Love" (1995).

After wending his way through a number of lower-profile features and several guest starring stints on the small screen, Cryer elevated his status when he joined "Two and a Half Men," a raunchy comedy that turned into a huge ratings winner for CBS, even though it suffered from the unpredictable behavior of star Sheen. Still, Cryer was able to weather that particular storm - and win an Emmy for his sitcom work in 2012 - while managing to escape the confines of being identified solely as the goofy and eccentric "Duckie."

Born Jonathan Niven Cryer in New York City on April 16, 1965, Cryer's parents were actors Gretchen Cryer, a stage actress and co-author of the popular musical "I'm Getting My Act Together and Taking It On the Road" (1975), and David Cryer, whom she divorced in 1968. Cryer made his earliest on-camera appearance a year later as a child model for a vitamin bottle label, but did not pursue an acting career in earnest until after graduation from the Bronx High School of Science in 1983.

Cryer's mother was reportedly supportive but cautious of her son's decision, but he soon allayed her fears by landing on Broadway in "Torch Song Trilogy" in the role of David, the adopted son of a single gay man. The role was originally played by Matthew Broderick, whom Cryer resembled closely. In fact, Cryer would later understudy for and eventually replace Broderick in the Broadway run of Neil Simon's "Brighton Beach Memoirs" in 1989.

Cryer made his theatrical feature debut in the 1984 coming-of-age comedy, "No Small Affair," in which he played a teenaged photographer (a role originally intended again for Broderick) who becomes infatuated with an older woman (Demi Moore). He followed this with a supporting turn as Fred Ward's son in an impressive PBS production of Katherine Porter's "Noon Wine" (1985), as well as a supporting role as the nerdy son of a middle-class family targeted by teen pranksters in Robert Altman's much-loathed "O.C. and Stiggs" (1987).

The following year, he caught the attention of audiences and critics alike as Duckie, the hopelessly romantic best friend of Molly Ringwald's waifish heroine in John Hughes' "Pretty in Pink." Cryer's animated performance - highlighted by a show-stopping lip-sync to an Otis Redding tune in Annie Potts' record store - captured the hearts of many of the film's teenage fans, who adamantly wished that Ringwald end up with Duckie at the film's conclusion, rather than Andrew McCarthy's wan pretty-boy hero (which was the original conclusion in Hughes' shooting script, but was changed by request of the producers). Cryer's association with the character was an amicable one, and he even repeated the role for an episode of "Mr. Show" (HBO, 1995-98).

Cryer's post-Duckie film career was a spotty one; attempts to fashion him into a teen heartthrob in "Morgan Stewart's Coming Home" (1987) and "Hiding Out" (1987) were largely ignored, and roles that broke that mold - such as a punk stuck in the Midwest in Penelope Spheeris' "Dudes" (1987) and as the villainous son of Lex Luthor in "Superman IV: The Quest for Peace" (1987) - went unseen by large audiences. He scored with critics as a young Greek baker who becomes the agent to a major Hollywood star in "The Famous Teddy Z," a sitcom created by Hugh Wilson of "WKRP in Cincinnati" (CBS, 1978-1982), but the show unfortunately never caught on with viewers.

Like many of the young actors who came to prominence in the mid-1980s, Cryer settled into a string of lower profile projects for most of the 1990s. He scored a hit alongside his future "Two and a Half Men" co-star Charlie Sheen in the broad comedy "Hot Shots!" but was more frequently seen in offbeat projects like "Heads" (1993), a dark comedy about a nebbish newspaper proof reader who becomes involved in a string of decapitation murders. Cryer also returned to television work with "Partners" (Fox, 1995), a short-lived romantic comedy about architects vying for the affection of the same girl. Cryer was reportedly asked to audition for the role of Chandler on "Friends" (NBC, 1994-2004), but due to a commitment to a play in London, was unable to submit his video audition in time, much to the relief of then unknown actor Matthew Perry.

Cryer went behind the camera as co-scripter of the independent comedy "The Pompatus of Love" (1996), which performed moderately well on the art house and festival circuits; more roles in obscure indies followed ("Plan B," 1997), as well as a second screenplay (with Richard Schenkman) for the little-seen "Went To Coney Island on a Mission from God Be Back by Five" (2000), for which he took top billing and co-produced. The picture took home the Audience Award at the Austin Film Festival in 1998. Meanwhile, he returned to sitcoms in the workplace comedy "Getting Personal" (Fox, 1998), which, despite a cast that included Vivica A. Fox and Elliot Gould, folded after just 17 episodes. He also tread the boards again in New York and Los Angeles productions of "900 Oneonta" in 1999. That same year, he married actress Sarah Trigger, with whom he had a son, Charlie Austin, in 2000.

With "The Trouble With Normal" (ABC, 2000-01), Cryer was one of four deeply paranoid young men who sought help in a therapy group run by Paget Brewster (Cryer's close friend in real life). He also began lending his voice to several animated projects, including "Hey Joel" (VH1, 2003), an animated talk show created by writer Joel Stein (who expressed considerable embarrassment over the project) and "American Dad" (Fox, 2005- ). In 2003, Cryer was cast alongside Charlie Sheen as brothers and polar opposites on the CBS comedy "Two and a Half Men." The premise, which had Cryer's anxiety-prone chiropractor move in with his young son (Angus T. Jones) into unrepentant bachelor Sheen's house, caught on with audiences, thanks to an unbeatable time slot on Monday night, its unabashedly bawdy humor, and the interplay between its three male leads.

The show provided a shot in the arm for both Sheen and Cryer's careers; both received Emmy nods for their work (Cryer was nominated twice in 2006 and 2007). The actor even stepped behind the cameras to direct an episode of the series in 2007.

In 2004, Cryer and Trigger divorced, which ironically left him the single father of a male son like his "Men" character, Alan Harper. The status did not last long. He announced his engagement to actress and television reporter Lisa Joyner on "The Tonight Show with Jay Leno" (NBC, 1992-2014) in January 2007. The couple went on to wed in June of that same year. Meanwhile, Cryer received more Emmy recognition for "Two and a Half Men;" including a 2008 nomination and a 2009 win for Best Supporting Actor in a Comedy Series. He followed with two more nominations in the category for 2010 and 2011. The latter nomination came after a rather trying year for all those involved in "Two and a Half Men." While Charlie Sheen had always been rather unpredictable, thanks in large part to his chemical addictions, the star went overboard after voluntarily taking a break from the show to enter rehab in February 2010. Just eight months later, Sheen was arrested in the Plaza Hotel for property damage, only to be taken to Cedars-Sinai three months after that for an alleged drug overdose that was publicly called "severe abdominal pains." What followed was a months-long public war of words between Sheen and show creator Chuck Lorre that culminated in Sheen's firing in March 2011.

Two months later, the show hired Ashton Kutcher as his replacement. Through it all, Cryer remained above the fray and refrained from public comment despite numerous questions regarding Sheen's outbursts - one of which involved Sheen calling Cryer a "traitor" and a "troll." But as it turned out, Cryer had the last laugh in 2012 when he won an Emmy Award for playing Alan Harper in the Outstanding Lead Actor in a Comedy Series category.